Electrospray ionization tandem mass spectrometry of 4-aryl-3,4-dihydrocoumarins

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Autor(es): dc.contributorUniversidade de São Paulo (USP)-
Autor(es): dc.contributorand Technology-
Autor(es): dc.contributorUniversidade Estadual Paulista (UNESP)-
Autor(es): dc.contributorUniversity of Victoria-
Autor(es): dc.creatorDias, Herbert J.-
Autor(es): dc.creatorSantos, William H.-
Autor(es): dc.creatorFilho, Luis C. S.-
Autor(es): dc.creatorCrevelin, Eduardo J.-
Autor(es): dc.creatorMcIndoe, J. Scott-
Autor(es): dc.creatorVessecchi, Ricardo-
Autor(es): dc.creatorCrotti, Antônio E. M.-
Data de aceite: dc.date.accessioned2025-08-21T22:34:38Z-
Data de disponibilização: dc.date.available2025-08-21T22:34:38Z-
Data de envio: dc.date.issued2025-04-29-
Data de envio: dc.date.issued2024-07-01-
Fonte completa do material: dc.identifierhttp://dx.doi.org/10.1002/jms.5062-
Fonte completa do material: dc.identifierhttps://hdl.handle.net/11449/296940-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/11449/296940-
Descrição: dc.descriptionWe have investigated the gas-phase fragmentation reactions of 11 synthetic 4-aryl-3,4-dihydrocoumarins by electrospray ionization tandem mass spectrometry (ESI-MS/MS) on a quadrupole-time-of flight (Q-TOF) hybrid mass spectrometer. We have also estimated thermochemical data for the protonated coumarins (precursor ion A) and product ion structures by computational chemistry at a B3LYP level of theory to establish the ion structures and to rationalize the fragmentation pathways. The most abundant ions in the product ion spectra of coumarins 1–11 resulted from C8H8O2, CO2, C4H4O3, C8H10O3, C8H8O2, and CH3OH eliminations through retro-Diels–Alder (RDA) reactions, remote hydrogen rearrangements (β-eliminations), and β-lactone ring contraction. Although the investigated coumarins shared most of the fragmentation pathways, formation of a benzylic product ion and its corresponding tropylium ion was diagnostic of the substituents at ring C. The thermochemical data revealed that the nature and position of the substituents at ring C played a key role in the formation of this product ion and determined its relative intensity in the product ion spectrum. The results of this study contribute to knowledge of the gas-phase ion chemistry of this important class of organic compounds.-
Descrição: dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)-
Descrição: dc.descriptionDepartment of Chemistry Faculty of Philosophy Science and Letters at Ribeirão Preto University of São Paulo-
Descrição: dc.descriptionGoiano Federal Institute of Education Science and Technology Campus Urutaí-
Descrição: dc.descriptionDepartment of Chemistry Faculty of Sciences at Bauru São Paulo State University-
Descrição: dc.descriptionDepartment of Chemistry University of Victoria-
Descrição: dc.descriptionDepartment of Chemistry Faculty of Sciences at Bauru São Paulo State University-
Descrição: dc.descriptionCNPq: 310648/2022-0-
Idioma: dc.languageen-
Relação: dc.relationJournal of Mass Spectrometry-
???dc.source???: dc.sourceScopus-
Palavras-chave: dc.subjectarylcoumarins-
Palavras-chave: dc.subjectbenzylic ions-
Palavras-chave: dc.subjectcomputational chemistry-
Palavras-chave: dc.subjectelectronic effects-
Palavras-chave: dc.subjecttropylium ions-
Título: dc.titleElectrospray ionization tandem mass spectrometry of 4-aryl-3,4-dihydrocoumarins-
Tipo de arquivo: dc.typelivro digital-
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